16461-71-5

Basic information

• Product Name: 2-azido-2-phenylacetyl chloride
• Synonyms: 2-azido-2-phenylacetyl chloride;α-Azidobenzeneacetic acid chloride;Einecs 240-509-7
• CAS NO: 16461-71-5
• Molecular Formula: C₈H₆ClN₃O
• Molecular Weight: 195.60574
• EINECS: 240-509-7
• Mol File: 16461-71-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-azido-2-phenylacetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-azido-2-phenylacetyl chloride(16461-71-5)
• EPA Substance Registry System: 2-azido-2-phenylacetyl chloride(16461-71-5)

Safety Data

• Hazardous Substances Data: 16461-71-5(Hazardous Substances Data)

Usage

General Description

2-azido-2-phenylacetyl chloride is a chemical compound with the molecular formula C8H6ClN3O. It is a highly reactive and potentially explosive compound that is commonly used in organic synthesis as a reagent for introducing the azide functional group into various organic molecules. It is often used in the preparation of azido-substituted amides, which are important intermediates in the synthesis of pharmaceutical compounds and advanced materials. Due to its explosive nature, 2-azido-2-phenylacetyl chloride must be handled with extreme caution and under strict safety protocols in a controlled laboratory environment.

InChI:InChI=1/C8H6ClN3O/c9-8(13)7(11-12-10)6-4-2-1-3-5-6/h1-5,7H

Upstream product

• 4870-65-9 2-bromophenylacetic acid 
• 29289-35-8 2-azido-2-phenylacetic acid 

Downstream Products

• 28357-46-2 azidocillin 
• 80653-95-8 benzyl 6-(α-azido-phenylacetamido)-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate 
• 59858-25-2 D,L-alpha-azidophenylacetic acid trimethylsilyl ester 
• 916599-59-2 α-azidophenylacetonitrile 
• 279676-21-0 (+/-)-2-azido-2-phenylacetamide 

Relevant articles and documents

Nitrile biotransformations for the practical synthesis of highly enantiopure azido carboxylic acids and amides, 'click' to functionalized chiral triazoles and chiral β-amino acids

Under very mild conditions, biotransformations of racemic azido nitriles using Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole-cell catalyst, afforded highly enantiopure, (R)-α-arylmethyl- and (+)-α-cyclohexylmethyl-β-azidopropanoic acids and their (S)- and (-)-carboxamide derivatives in excellent yields. The resulting functionalized chiral organoazides were converted in a straightforward fashion to a pair of antipodes of α-benzyl-β-amino acids (R)-13 and (S)-13. Azido carboxamide (S)-11a and azido carboxylic acid (R)-12a underwent 'click' reactions with diethyl acetylenedicarboxylate and phenylacetylene to produce functionalized chiral triazoles 14 and 15, respectively. The easy preparation of the starting nitrile substrates, highly efficient and enantioselective biotransformation reactions, and versatile utility of the resulting functionalized azido carboxylic acids and amide derivatives, render this method very attractive and practical in organic synthesis.

6α, β-Substituted penicillin derivatives

Novel 6-methoxy and 6-thioalkyl-6-acylamido-penicillanic acids and their non-toxic pharmaceutically-acceptable salts, esters and amides which are useful as antibiotics. The products are prepared by treating an ester of 6-substituted-6-aminopenicillanic acid with an acylating agent followed by removal of the ester group. Also disclosed are novel intermediates.

SEMISYNTHETIC PENICILLINS. 3. AMINOPENICILLINS VIA AZIDOPENICILLINS.

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